AR040414A1 - AMINO ACETONITRILE COMPOUNDS, PROCESS FOR PREPARATION AND COMPOSITION FOR PARASITE CONTROL - Google Patents

AMINO ACETONITRILE COMPOUNDS, PROCESS FOR PREPARATION AND COMPOSITION FOR PARASITE CONTROL

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Publication number
AR040414A1
AR040414A1 AR20030102158A ARP030102158A AR040414A1 AR 040414 A1 AR040414 A1 AR 040414A1 AR 20030102158 A AR20030102158 A AR 20030102158A AR P030102158 A ARP030102158 A AR P030102158A AR 040414 A1 AR040414 A1 AR 040414A1
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Argentina
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unsubstituted
substituted
many times
halo
alkyl
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AR20030102158A
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Spanish (es)
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Novartis Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/26—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups, amino groups and singly-bound oxygen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms

Abstract

Compuestos de fórmula (1) y opcionalmente enantiómeros de los mismos. Los ingredientes activos tienen propiedades plaguicidas convenientes. Estos son adecuados para controlar parásitos en animales de sangre caliente. Reivindicación 1: Un compuesto de fórmula (1) en donde Ar significa arilo o hetarilo, que está insubstituido o substituido una o muchas veces, en donde los substituyentes pueden ser independientes unos de otros y se seleccionan a partir del grupo que consiste en halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6, alcoxi C1-6, halo-alcoxi C1-6, alquenilo C2-6, halo-alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, cicloalcoxi C3-6, cicloalquilamino C3-6, cicloalquiltio C3-6, alqueniloxi C2-6, halo-alqueniloxi C2-6,alquiltio C1-6, halo-alquiltio C1-6, alquilsulfoniloxi C1-6, halo-alquilsulfoniloxi C1-6, alquilsulfinilo C1-6, halo-alquilsulfinilo C1-6, alquilsulfonilo C1-6, halo-alquilsulfonilo C1-6, alqueniltio C2-6, halo-alqueniltio C2-6, alquenilsulfinilo C2-6, halo-alquenilsulfinilo C2-6, alquenilsulfonilo C2-6, halo-alquenilsulfonilo C2-6, alquilamino C1-6, di-alquilamino C1-6, alquilsulfonilamino C1-6, halo-alquilsulfonilamino C1-6, alquilcarbonilo C1-6, halo-alquilcarbonilo C1-6, alcoxicarbonilo C1-6, alquilaminocarbonilo C1-6, di-alquilamino-carbonilo C1-6, fenilamino que está insubstituido o substituido una o muchas veces, arilsulfonilo que está insubstituido o substituido una o muchas veces, fenilcarbonilo que está insubstituido o substituido una o muchas veces, fenilmetoximino que está insubstituido o substituido una o muchas veces; fenilhidroximetilo que está insubstituido o substituido una o muchas veces, 1-fenil-1-hidroxietilo que está insubstituido o substituido una o muchas veces, fenilclorometilo que está insubstituido o substituido una o muchas veces, fenilcianometilo que está insubstituido o substituido una o muchas veces, fenilo que está insubstituido o substituido una o muchas veces, fenoxi que está insubstituido o substituido una o muchas veces, fenilacetilenilo que está insubstituido o substituido una o muchas veces y piridiloxilo que está insubstituido o substituido una o muchas veces, en donde los substituyentes pueden ser independientes unos de otros y se seleccionan a partir del grupo que consiste en halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6, alcoxi C1-6, halo-alcoxi C1-6, alquiltio C1-6, halo-alquiltio C1-6, alquilsulfinilo C1-6, halo-alquilsulfinilo C1-6, alquilsulfonilo C1-6, halo-alquilsulfonilo C1-6, alquilamino C1-6 y di-alquilamino C1-6; R1 significa hidrógeno,alquilo C1-6, halo-alquilo C1-6, alilo o alcoximetilo C1-6; R2, R3, R4, R5 y R6 son, independientemente unos de otros, hidrógeno, halógeno, alquilo C1-6 que está insubstituido o substituido una o muchas veces, alquenilo C2-6 que está insubstituido o substituido una o muchas veces, alquinilo C2-6 que está insubstituido o substituido una o muchas veces, alcoxi C1-6 que está insubstituido o substituido una o muchas veces, en donde los substituyentes pueden ser independientes unos de otros y se seleccionan a partir del grupo que consiste en halógeno, alcoxi C1-6, halo-alcoxi C1-6; cicloalquilo C3-6 que está insubstituido o substituido una o muchas veces, en donde los substituyentes pueden ser independientes unos de otros y se seleccionan a partir del grupo que consiste en halógeno y alquilo C1-6; o fenilo que está insubstituido o substituido una o muchas veces, en donde los substituyentes pueden ser independientes unos de otros y se seleccionan a partir del grupo que consiste en halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6,alcoxi C1-6, halo-alcoxi C1-6, alquiltio C1-6, halo-alquiltio C1-6, alquilsulfinilo C1-6, halo- alquilsulfinilo C1-6, alquilsulfonilo C1-6, halo-alquilsulfonilo C1-6, alquilamino C1-6 o di-alquilamino C1-6; o R2 y R3 significan juntos alquileno C2-6; R7 significa hidrógeno o alquilo C1-6; ya sea que R8 significa fenilcarbonilo que está insubstituido o substituido una o muchas veces, fenoxicarbonilo que está insubstituido o substituido una o muchas veces, benciloxicarbonilo que está insubstituido o substituido una o muchas veces, fenil-alquilo C1-6 que está insubstituido o substituido una o muchas veces, fenoxi-alquilo que está insubstituido o substituido una o muchas veces, fenil-alcoxi C1-6 que está insubstituido o substituido una o muchas veces, hetariloxicarbonilo que está insubstituido o substituido una o muchas veces, alquilcarboxi C1-6; fenilcarboxi que está insubstituido o substituido una o muchas veces, bencilcarboxi que está insubstituido o substituido una o muchas veces, fenilcarboxamido que está insubstituido o substituido una o muchas veces, alquilcarboxamido C1-6, alquiloxicarboxamido C1-6; feniloxicarboxamido que está insubstituido o substituido una o muchas veces, fenilaminocarboxi que está insubstituido o substituido una o muchas veces, feniloxicarboxi que está insubstituido o substituido una o muchas veces, fenilaminocarboxamido que está insubstituido o substituido una o muchas veces, alquiloxi C1-6-alquiloxi C1-6, hidroxi-alquilo C1-6, alquiloxi C1-6-alquilo C1-6, alquilaminocarbonilo C1-6, (alquilo C1-6)2aminocarbonilo; fenilaminocarbonilo que está insubstituido o substituido una o muchas veces, alquiltio C1-6-alquilo C1-6; feniltio-alquilo C1-6 que está insubstituido o substituido una o muchas veces, fenilmetoximino que está insubstituido o substituido una o muchas veces, fenilhidroximetil que está insubstituido o substituido una o muchas veces, 1-fenil-1-hidroxietil que está insubstituido o substituido una o muchas veces,fenilclorometilo que está insubstituido o substituido una o muchas veces, o fenilcianometilo que está insubstituido o substituido una o muchas veces, en donde los substituyentes pueden ser independientes unos de otros y se seleccionan a partir del grupo que consiste en R9; y R8' significa hidrógeno; o R8 y R8' significan juntos alquileno C1-4 que está insubstituido o substituido una o muchas veces por alquilo C1-4, en donde uno o dos átomos de carbono pueden ser reemplazados por oxígeno; R9 significa halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6, alcoxi C1-6, halo-alcoxi C1-6, alquenilo C2-6, halo-alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, cicloalquiloxi C3-6, cicloalquilamino C3-6, cicloalquiltio C3-6, alqueniloxi C2-6, halo-alqueniloxi C2-6, alquiltio C1-6, halo-alquiltio C1-6, alquilsulfoniloxi C1-6, halo-alquilsulfoniloxi C1-6, alquilsulfinilo C1-6, halo-alquilsulfinilo C1-6, alquilsulfonilo C1-6, halo-alquilsulfonilo C1-6, alqueniltio C2-6, halo-alqueniltio C2-6, alquenilsulfinilo C2-6, halo-alquenilsulfinilo C2-6, alquenilsulfonilo C2-6, halo-alquenilsulfonilo C2-6, alquilamino C1-6, di-alquilamino C1-6, alquilsulfonilamino C1-6, halo-alquilsulfonilamino C1-6, alquilcarbonilo C1-6, halo-alquilcarbonilo C1-6, alcoxicarbonilo C1-6, alquilaminocarbonilo C1-6, di-alquilaminocarbonilo C1-6, fenilamino que está insubstituido o substituido una o muchas veces, fenilcarbonilo que está insubstituido o substituido una o muchas veces, fenilmetoximino que está insubstituido o substituido una o muchas veces; fenilhidroximetilo, 1-fenil-1-hidroxietilo que está insubstituido o substituido una o muchas veces, fenilclorometilo que está insubstituido o substituido una o muchas veces, fenilcianometilo que está insubstituido o substituido una o muchas veces, fenilo que está insubstituido o substituido una o muchas veces, fenoxi que está insubstituido o substituido una o muchas veces, feniltio que está insubstituido o substituido una o muchas veces, fenilacetilenilo, o piridiloxilo que está insubstituido o substituido una o muchas veces, en donde los substituyentes pueden ser independientes unos de otros y se seleccionan a partir del grupo que consiste en halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6, alcoxi C1-6, halo- alcoxi C1-6, alquiltio C1-6, halo-alquiltio C1-6, alquilsulfinilo C1-6, halo-alquilsulfinilo C1-6, alquilsulfonilo C1-6 y halo-alquilsulfonilo C1-6; W significa O, S, S(O2) o N(R7) a significa 1, 2, 3 o 4; b significa 0, 1, 2, 3 o 4; y n es 0, 1, 2 o 3. Reivindicación 33: Un proceso para la preparación de los compuestos de la fórmula (1), respectivamente en forma libre o en forma de sal, de acuerdo con la reivindicación 1, mediante el cual se hace reaccionar un compuesto de la fórmula (2), el cual es conocido o se puede producir de una manera análoga a los compuestos conocidos correspondientes, y en donde R1, R2, R3, R4, R5, R6, R8, R8', R9, W, a, b y n se definen como se dan para la fórmula (1), con un compuesto de la fórmula (3), el cual es conocido o se puede preparar de una manera análoga a los compuestos conocidos correspondientes, y en donde Ar se define como se da para la fórmula (1), y Q es un grupo saliente, opcionalmente en la presencia de un catalizador básico, y si se desea, un compuesto de la fórmula (1) que se pueda obtener de otra manera, respectivamente en forma libre o en forma de sal, se convierte en otro compuesto de fórmula (1), se separa una mezcla de isómeros que se pueda obtener de acuerdo con el método, y se aísla el isómero deseado, y/o un compuesto libre de la fórmula (1) que se pueda obtener de acuerdo con el método, se convierte en una sal, o una sal de compuesto de la fórmula (1) que se pueda obtener de acuerdo con el método se convierte en el compuesto libre de la fórmula (1) o en otra sal.Compounds of formula (1) and optionally enantiomers thereof. The active ingredients have convenient pesticidal properties. These are suitable for controlling parasites in warm-blooded animals. Claim 1: A compound of formula (1) wherein Ar means aryl or heteroaryl, which is unsubstituted or substituted one or many times, wherein the substituents may be independent of each other and are selected from the group consisting of halogen, nitro, cyano, C1-6 alkyl, halo- C1-6 alkyl, C1-6 alkoxy, halo C1-6 alkoxy, C2-6 alkenyl, C2-6 halo-alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 cycloalkoxy, C3-6 cycloalkylamino, C3-6 cycloalkylthio, C2-6 alkenyloxy, C2-6 halo-alkenyloxy, C1-6 alkylthio, halo- C 1-6 alkylthio, C1-6 alkylsulfonyloxy, haloC 1-6 alkylsulfonyloxy , C1-6 alkylsulfinyl, halo C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, halo C1-6 alkylsulfonyl, C2-6 alkenylthio, C2-6 alkenylthio, C2-6 alkenylsulfinyl, C2-6 halo-alkenylsulfinyl, alkenylsulfonyl C2-6, C2-6 halo-alkenylsulfonyl, C1-6 alkylamino, C1-6 alkylamino, C1-6 alkylsulfonylamino, C1-6 halo-alkylsulfonylamino, C1-6 alkylcarbonyl, halo-alkylcarboni C1-6, C1-6 alkoxycarbonyl, C1-6 alkylaminocarbonyl, di- C 1-6 alkylaminocarbonyl, phenylamino that is unsubstituted or substituted one or many times, arylsulfonyl that is unsubstituted or substituted one or many times, phenylcarbonyl that is unsubstituted or substituted once or many times, phenylmethoximin that is unsubstituted or substituted once or many times; phenylhydroxymethyl that is unsubstituted or substituted one or many times, 1-phenyl-1-hydroxyethyl that is unsubstituted or substituted one or many times, phenylchloromethyl that is unsubstituted or substituted one or many times, phenylcyanomethyl that is unsubstituted or substituted one or many times, phenyl that is unsubstituted or substituted one or many times, phenoxy that is unsubstituted or substituted one or many times, phenylacetylenyl that is unsubstituted or substituted once or many times and pyridyloxy which is unsubstituted or substituted one or many times, where the substituents may be independent from each other and are selected from the group consisting of halogen, nitro, cyano, C1-6 alkyl, halo- C1-6 alkyl, C1-6 alkoxy, halo C1-6 alkoxy, C1-6 alkylthio, halo -C 1-6 alkylthio, C 1-6 alkylsulfinyl, halo C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfonyl, C 1-6 alkylamino and C 1-6 alkylamino; R1 means hydrogen, C1-6 alkyl, halo- C1-6 alkyl, allyl or C1-6 alkoxymethyl; R2, R3, R4, R5 and R6 are, independently of one another, hydrogen, halogen, C1-6 alkyl that is unsubstituted or substituted one or many times, C2-6 alkenyl that is unsubstituted or substituted one or many times, C2 alkynyl -6 which is unsubstituted or substituted one or many times, C1-6 alkoxy that is unsubstituted or substituted one or many times, wherein the substituents may be independent of each other and are selected from the group consisting of halogen, C1 alkoxy -6, haloC 1-6 alkoxy; C3-6 cycloalkyl that is unsubstituted or substituted one or many times, wherein the substituents may be independent of each other and are selected from the group consisting of halogen and C1-6 alkyl; or phenyl that is unsubstituted or substituted one or many times, wherein the substituents may be independent of each other and are selected from the group consisting of halogen, nitro, cyano, C1-6 alkyl, halo- C1-6 alkyl, C1-6 alkoxy, halo- C1-6 alkoxy, C1-6 alkylthio, halo C1-6 alkylthio, C1-6 alkylsulfinyl, halo- C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 halo alkylsulfonyl, C1 alkylamino -6 or C1-6 di-alkylamino; or R2 and R3 together mean C2-6 alkylene; R7 means hydrogen or C1-6 alkyl; Either R8 means phenylcarbonyl that is unsubstituted or substituted one or many times, phenoxycarbonyl that is unsubstituted or substituted once or many times, benzyloxycarbonyl that is unsubstituted or substituted once or many times, phenyl-C1-6 alkyl that is unsubstituted or substituted. or many times, phenoxy-alkyl that is unsubstituted or substituted one or many times, phenyl-C1-6 alkoxy that is unsubstituted or substituted one or many times, hetaryloxycarbonyl that is unsubstituted or substituted one or many times, C1-6 alkylcarboxy; phenylcarboxy that is unsubstituted or substituted one or many times, benzylcarboxy that is unsubstituted or substituted one or many times, phenylcarboxamide that is unsubstituted or substituted one or many times, C1-6 alkylcarboxamide, C1-6 alkyloxycarboxamide; phenyloxycarboxamide that is unsubstituted or substituted one or many times, phenylaminocarboxy that is unsubstituted or substituted one or many times, phenyloxycarboxy that is unsubstituted or substituted one or many times, phenylaminocarboxamide that is unsubstituted or substituted one or many times, C1-6 alkyloxy C1-6, hydroxy-C1-6 alkyl, C1-6 alkyloxy-C1-6 alkyl, C1-6 alkylaminocarbonyl, (C1-6 alkyl) 2-aminocarbonyl; phenylaminocarbonyl that is unsubstituted or substituted one or many times, C1-6 alkylthio-C1-6 alkyl; phenylthio-C 1-6 alkyl that is unsubstituted or substituted one or many times, phenylmethoximino that is unsubstituted or substituted one or many times, phenylhydroxymethyl that is unsubstituted or substituted once or many times, 1-phenyl-1-hydroxyethyl that is unsubstituted or substituted once or many times, phenylchloromethyl that is unsubstituted or substituted once or many times, or phenylcyanomethyl that is unsubstituted or substituted once or many times, wherein the substituents may be independent of each other and are selected from the group consisting of R9; and R8 'means hydrogen; or R8 and R8 'together mean C1-4 alkylene which is unsubstituted or substituted once or many times by C1-4 alkyl, wherein one or two carbon atoms can be replaced by oxygen; R9 means halogen, nitro, cyano, C1-6 alkyl, halo- C1-6 alkyl, C1-6 alkoxy, halo C1-6 alkoxy, C2-6 alkenyl, halo C2-6 alkenyl, C2-6 alkynyl, cycloalkyl C3-6, C3-6 cycloalkyloxy, C3-6 cycloalkylamino, C3-6 cycloalkylthio, C2-6 alkenyloxy, C2-6 halo-alkenyloxy, C1-6 alkylthio, C1-6 halo-alkylthio, C1-6 alkylsulfonyloxy, halo- C 1-6 alkylsulfonyloxy, C 1-6 alkylsulfinyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfonyl, C 2-6 alkenylthio, C 2-6 alkenylthio, C2-6 alkenylsulfinyl, C2 halo alkylsulfinyl -6, C2-6 alkenylsulfonyl, C2-6 halo-alkenylsulfonyl, C1-6 alkylamino, C1-6 alkylamino, C1-6 alkylsulfonylamino, haloC 1-6 alkylsulfonylamino, C1-6 alkylcarbonyl, haloC 1-6 alkylcarbonyl , C1-6 alkoxycarbonyl, C1-6 alkylaminocarbonyl, C1-6 di-alkylaminocarbonyl, phenylamino that is unsubstituted or substituted one or many times, phenylcarbonyl that is unsubstituted or substituted one or many times, phenylmethoximin which is unsubstituted or substituted once or many times; phenylhydroxymethyl, 1-phenyl-1-hydroxyethyl that is unsubstituted or substituted one or many times, phenylchloromethyl that is unsubstituted or substituted one or many times, phenylcyanomethyl that is unsubstituted or substituted one or many times, phenyl that is unsubstituted or substituted one or many sometimes, phenoxy that is unsubstituted or substituted one or many times, phenylthio that is unsubstituted or substituted one or many times, phenylacetylenyl, or pyridyloxy which is unsubstituted or substituted one or many times, where the substituents may be independent of each other and be selected from the group consisting of halogen, nitro, cyano, C1-6 alkyl, halo- C1-6 alkyl, C1-6 alkoxy, halo- C1-6 alkoxy, C1-6 alkylthio, C1-6 halo-alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl and C 1-6 alkylsulfonyl; W means O, S, S (O2) or N (R7) a means 1, 2, 3 or 4; b means 0, 1, 2, 3 or 4; and n is 0, 1, 2 or 3. Claim 33: A process for the preparation of the compounds of the formula (1), respectively in free form or in salt form, according to claim 1, by which it is made reacting a compound of the formula (2), which is known or can be produced in a manner analogous to the corresponding known compounds, and wherein R1, R2, R3, R4, R5, R6, R8, R8 ', R9, W, a, b and n are defined as given for formula (1), with a compound of formula (3), which is known or can be prepared in a manner analogous to the corresponding known compounds, and wherein Ar is defined as given for formula (1), and Q is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula (1) that can be obtained otherwise, respectively in free form or in salt form, it becomes another compound of formula (1), a mixture of isomers that can be obtained is separated according to the method, and the desired isomer is isolated, and / or a free compound of the formula (1) that can be obtained according to the method, is converted into a salt, or a salt of compound of the formula ( 1) that can be obtained according to the method becomes the free compound of the formula (1) or another salt.

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AU2009307736B2 (en) 2008-10-21 2015-02-05 Boehringer Ingelheim Animal Health USA Inc. Thioamide compounds, method of making and method of using thereof
LT3050874T (en) 2008-11-14 2019-04-10 Merial Inc. Enantiomerially enriched aryloazol-2-yl cyanoethylamino paraciticidal compounds
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